A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines

N. Elders, R.F. Schmitz, F.J.J. de Kanter, E. Ruijter, M.B. Groen, R.V.A. Orru

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

(Chemical Equation Presented) A multicomponent reaction between α-acidic isonitriles, primary amines, and carbonyl compounds was studied using 14 different solvents. Depending on the isocyanide that was used, optimal yields for the three-component synthesis of 2H-2-imidazolines were observed in different solvents. The solvents could be used as purchased, and in situ preformation of the imine was not required. By selecting the appropriate solvent, it was possible to considerably expand the range of compatible isocyanides toward less α-acidic isocyanides. Further process simplification was achieved by performing the reaction at higher concentrations and avoiding purification by column chromatography, resulting in a fast, easy to perform, and resource-efficient protocol for this three-component reaction. © 2007 American Chemical Society.
Original languageEnglish
Pages (from-to)6135-42
JournalJournal of Organic Chemistry
Volume72
Issue number16
DOIs
Publication statusPublished - 2007

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Cyanides
Carbonyl compounds
Column chromatography
Imines
Amines
Purification
2-imidazoline

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Elders, N. ; Schmitz, R.F. ; de Kanter, F.J.J. ; Ruijter, E. ; Groen, M.B. ; Orru, R.V.A. / A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 16. pp. 6135-42.
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A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines. / Elders, N.; Schmitz, R.F.; de Kanter, F.J.J.; Ruijter, E.; Groen, M.B.; Orru, R.V.A.

In: Journal of Organic Chemistry, Vol. 72, No. 16, 2007, p. 6135-42.

Research output: Contribution to JournalArticleAcademicpeer-review

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AB - (Chemical Equation Presented) A multicomponent reaction between α-acidic isonitriles, primary amines, and carbonyl compounds was studied using 14 different solvents. Depending on the isocyanide that was used, optimal yields for the three-component synthesis of 2H-2-imidazolines were observed in different solvents. The solvents could be used as purchased, and in situ preformation of the imine was not required. By selecting the appropriate solvent, it was possible to considerably expand the range of compatible isocyanides toward less α-acidic isocyanides. Further process simplification was achieved by performing the reaction at higher concentrations and avoiding purification by column chromatography, resulting in a fast, easy to perform, and resource-efficient protocol for this three-component reaction. © 2007 American Chemical Society.

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